Andre Villas-Boas has found his feet at Tottenham in the last month and the Spurs manager is ready to test the club's ambition as they prepare for the January transfer window.

Daniel Levy, the Tottenham chairman, considers himself a transfer window specialist. Nothing gets his juices going more than the thrill of a deadline day haggle, the opportunity to strike a deal and get one over rivals’ executives.

Yet his desire for a bargain and tendency to move the goalpoasts has frustrated many of his managers - past and present.

While Villas-Boas publically plays down his ambitions for the January transfer window, he is already putting pressure on Levy in private to secure the signings that will aid Spurs’ push for a top-four finish this season. They currently sit fifth in the Premier League, level on points with fourth-placed Everton.

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In fact, Villas-Boas has told his superiors that the club could be challenging for the title had he been delivered his summer targets, which included Leandro Damiao, Joao Moutinho and Hulk.

The collapse of the Moutinho deal on the final day of the transfer window was of particular frustration to Villas-Boas, who had made the playmaker his top target.

The move fell through at the last minute despite Spurs agreeing a £22 million fee with Porto earlier in the day - all after Villas-Boas was told Moutinho would arrive once the Londoners sold Rafael van der Vaart to Hamburg.

The Portuguese is in bullish mood as we approach the New Year and wants to add a creative midfielder and a winger to the squad.

Flexibility is not one of Villas-Boas’ strongest assets, and he is already pushing Levy to strike a January deal for Moutinho, even though he knows such a move is highly unlikely given Porto would demand close to £30m.

The question now is how much Levy is willing to back Villas-Boas in the transfer market, especially while the club attempt to finance the construction of a new £400m stadium.

The truth is that Villas-Boas will not be able to change Levy’s ways. He only needs to ask one of his three predecessors: Harry Redknapp, Juande Ramos or Martin Jol.

And while the day-to-day relationship between chairman and manager is reasonably strong, there are tensions over the club’s transfer strategy, with Villas-Boas feeling misled by promises made when he signed a three-year contract in the summer.

Emmanuel Adebayor was the only one of Spurs' summer signings laid out as a specific target by Villas-Boas. Deals for Jan Vertonghen, Gyfli Sigurdsson, Mousa Dembele, Clint Dempsey and Hugo Lloris were all driven by the chairman.

The likely outcome this time around is that Spurs will try to land their leading targets - the likes of Moutinho, Christian Eriksen and Shakhtar Donetsk star Willian - but Levy will once again refuse to break the bank for one player.

The January transfer window is historically less conducive to negotiating major transfers than the summer. Clubs are reluctant to allow their best players to leave halfway through the season, especially if they are playing in European competition,

Villas-Boas will continue to push Levy - and the manager has made it very clear which players he wants. He does not want to revert to the type of last-minute ‘deals’ like the one that saw Clint Dempsey arrive from Fulham on the last day of August.

It requires a fine balancing act to satisfy your boss while at the same time making sure you have the tools to do you job to the best of your ability. The next two months will tell us much about the future of the Villas-Boas and Levy partnership.Follow Greg Stobart on